As the well-off head in droves to the Hamptons for summer magic, the arty set are also gearing up to venture out of the enchanted island of Manhattan for a weekend of beachside art installations, events, and hobnobbing at this year’s ArtHamptons. In preparation for the hip Lower East Side gallery workers mixing with the fat wallets of Southampton, the fair has scheduled a slew of events geared toward both the pop-culture hipsters and cultural elite—albeit in entirely separate events. The Hamptonite shirts have Money & Art, an interactive Jackson Pollock installation and the honoring of seminal West Coast artist Ed Moses, while the skins get one half of Cheech and Chong, Kimora’s ex and a tea dance with Lady Bunny. Yet the fair promises each to mesh the “Hamptons glamorous art aficionados,” “art fair cognoscenti” and “art world luminaries” with lively conversation.

Bridging the gap is Lisa Jack’s photos of Barack Obama that she took when she was a freshman in college—because we all know how much arty types want to talk politics while in the Hamptons. Each of the events seems to be designed to enrage the opposing sector, which could set the stage for a very interesting vibe at this year’s ArtHamptons.

Red Grooms, Jackson in Action, 1997, 3-D lithograph; Courtesy of Marlborough Graphics. On view in The Persistence of Pollock, May 3 – July 28, 2012, at the Pollock-Krasner House and Study Center, East Hampton.

Pretty People Paint Pollock invites the platinum and VIPs to get a taste of the bohemian life—and make their own “Pollock.” Cardholders can help contribute to a giant drip painting that will be displayed amidst photos of Pollock at work, as well as the replica paintings from the 2000 biopic, in the lobby for the duration of the fair. Decidedly reducing Pollock’s life’s work to gestural mimicry is enough to make art historians wince, and displaying them next to declared replicas is just salt in their wounds.

Contrastly, we have the Arts Patron of the Year Award going to one the world’s most infamous stoners, Cheech Marin. Cheech’s collection of Chicano art is one of the world’s finest, gaining him traction in the art world, but also has become the driving force for the collector to share his passion and help curate Chicano art exhibitions at the museum level, including at LACMA, the Art Museum of South Texas in Corpus Christi and the Museum of Monterey. Anyone with money can collect art, but Cheech’s focus supports an under-credited movement, while bringing awareness of these artists for art world and public consumption. VIP’s can even attend Cheech’s “cool birthday bash” at the Polo Lounge.

The proclaimed art world luminaries can duke it out with the VIP greenbacks at Friday’s panel discussion, The Last Taboo: The Nexus Between Money and Art.” Moderated by Hamptons artist Dan Rizzle, this is the chance to let out your frustrations on the effects of money and art, before making amends to compromise to make it a mutually important relationship. If you’re convinced, artnet is also hosting a talk by Thomas Galbraith, discussing the return on investment of low and high art works, again translating art to money.

Lady Bunny, Mine’s Bigger Than Yours. Photo by Aaron Cobbett.

But perhaps what we can all agree on is how to kick back, have a few cocktails, and get our groove on. Lady Bunny, Manhattan nightlife celebrity and drag veteran, is making the trek to host the annual Empire State Pride Agenda Hamptons Tea Dance. The LGBT awareness fundraiser is in its 20th year, but makes its debut with ArtHamptons, taking over part of the art fair green for an afternoon of dancing and drinking with New York’s most glamorous drag queens. And both sides can end the weekend and meet hip-hop mogul and entrepreneur, Russell Simmons, as he talks about his Rush Foundation for the Arts at a VIP meet-and-greet hosted by the Hamptons Social Network.

The roster of ArtHamptons events seems to set the stage for an intriguing—and possibly even challenging—fair, questioning whether the fair itself believes that art is for everyone, or for their Platinum VIPs. Whether the event committee intended to bring up these issues or not, it is the Hamptons and we can all agree that a good way to ensure art camaraderie is plenty of beach time and free flowing champagne!